Cholesteryl laurate

Base Information

• Chemical Name: Cholesteryl laurate
• CAS No.: 1908-11-8
• Deprecated CAS: 137170-90-2
• Molecular Formula: C39H68O2
• Molecular Weight: 568.968
• European Community (EC) Number: 217-613-6
• NSC Number: 80701
• UNII: 3CV9B999WH
• DSSTox Substance ID: DTXSID90929731
• Nikkaji Number: J151.254D
• Wikidata: Q27257048
• Metabolomics Workbench ID: 34667
• Mol file: 1908-11-8.mol

Synonyms:Cholesteryl laurate;Cholesterol laurate;1908-11-8;Cholesteryl dodecanoate;Cholesterol, laurate;Dodecanoic acid, cholesteryl ester;CE(12:0);Cholesteryl dodecanoate (Laurate);cholest-5-en-3Beta-yl dodecanoate;Cholest-5-en-3-ol (3beta)-, 3-dodecanoate;12:0 Cholesteryl ester;[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] dodecanoate;Cholest-5-en-3.beta.-ol dodecanoate;3CV9B999WH;Cholest-5-en-3-beta-yl laurate;Cholest-5-en-3beta-ol dodecanoate;NSC-80701;Cholest-5-en-3-ol (3.beta.)-, dodecanoate;MFCD00021142;Cholesterol Dodecanoate;Cholesteryl lauric acid;CHOLESTERYLLAURATE;12:0 Cholesterol ester;Cholesteryl dodecanoic acid;cholest-5-en-3-yl laurate;UNII-3CV9B999WH;Lauric Acid Cholesterol Ester;SCHEMBL295198;Cholest-5-en-3-yl dodecanoate;Cholest-5-en-3b-ol dodecanoate;5-Cholesten-3.beta.-ol laurate;Dodecanoic acid cholesteryl ester;Dodecanoic Acid Cholesterol Ester;DTXSID90929731;CHEBI:183816;3.beta.-Dodecanoyloxycholest-5-ene;NSC80701;Cholest-5-en-3b-ol dodecanoic acid;EINECS 217-613-6;LMST01020001;NSC 80701;AKOS025310957;cholest-5-en-3beta-yl dodecanoic acid;Cholest-5-en-3beta-ol dodecanoic acid;HY-W127400;(3beta)-Cholest-5-en-3-ol dodecanoate;AS-63615;CHOLEST-5-EN-3-.BETA.-YL LAURATE;Cholest-5-en-3-ol (3beta)-, dodecanoate;(3beta)-Cholest-5-en-3-ol dodecanoic acid;CS-0185635;D95278;Cholest-5-en-3-ol (3.beta.)-, 3-dodecanoate;W-107736;Q27257048;Cholesteryl dodecanoate, >=98% (HPLC;detection at 205 nm)

Chemical Property of Cholesteryl laurate

Chemical Property:

• Melting Point: 91-92 °C
• Refractive Index: 1.508
• Boiling Point: 609.365 °C at 760 mmHg
• Flash Point: 321.494 °C
• PSA: 26.30000
• Density: 0.964 g/cm³
• LogP: 11.86050
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Hexanes (Slightly)
• XLogP3: 14.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 17
• Exact Mass: 568.52193141
• Heavy Atom Count: 41
• Complexity: 843

Purity/Quality:

98%,99%, ^*data from raw suppliers

CholesterolLaurate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CCC4C(C)CCCC(C)C)C)C
• Isomeric SMILES: CCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC[C@@H]4[C@H](C)CCCC(C)C)C)C
• Uses: Cholesterol laurate is a cholesterol (C432501) and fatty acid (L178550) derivative with antimycobacterial properties.

Technology Process of Cholesteryl laurate

There total 8 articles about Cholesteryl laurate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

lauric acid (143-07-7) + cholesterol (57-88-5) → cholesteryl laurate (1908-11-8)

Guidance literature:

With iron(III) chloride hexahydrate; In 1,3,5-trimethyl-benzene; for 12h; Reflux;

DOI:10.1055/s-0028-1083175

Reference yield:

n-dodecanoyl chloride (112-16-3) + cholesterol (57-88-5) → cholesteryl laurate (1908-11-8)

Guidance literature:

With chloroform;

Reference yield:

lauric acid (143-07-7) + cholesterol (57-88-5) → cholesteryl laurate (1908-11-8)

Guidance literature:

With toluene-4-sulfonic acid; benzene;

DOI:10.1021/ja01127a514

upstream raw materials:

lauric acid

cholesterol

n-dodecanoyl chloride

cholesterol

Refernces

• 1、 Weber, Nikolaus,Weitkamp, Petra,Mukherjee, Kumar D.. "Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst". . p. 67 - 71. Retrieved 2001.
• 2、 Komura, Kenichi,Ozaki, Akiyoshi,Ieda, Noboru,Sugi, Yoshihiro. "FeCl3·6H2O as a versatile catalyst for the esterification of steroid alcohols with fatty acids". experimental part. p. 3407 - 3410. Retrieved 2009/05/09.